The only time I've had an issue with using the keypad is during the prompt that goes something like, "In a few words, tell me what you're calling about."
Hitting zero repeatedly at that point is usually the only way through.
I was at the T-Mobile internet trucks in Asheville and the woman next to me was obviously stuck in some automated voice menu hell — you know when some one is sitting on the phone quietly listening to whatever the question “What can I help you with?” and then answering with one clear word. I saw her sitting there like that waiting, then respond clearly, “Disaster!” I’m going to guess the system didn’t have a way of handling that answer.